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I used to be a 335-pound liability. For 30 years, I was the “Last Man Standing” in the retail trenches—leading crews through Hurricane Sandy, blackouts, and 3:00 AM transformer explosions. I had the grit, and eventually, I had the $3M net worth to prove it. But I was also a walking “short squeeze.” My joints screamed, I snored like a freight train, and I was trading my health for a 401(k) I couldn’t even touch. […]
If you never spend your investment gains, what exactly are you investing for? This question hit me hard after a year of nonstop financial management, market volatility, and real estate turnover in 2025. I had done everything “right” from an investing perspective, yet I felt deprived. So I made a new financial rule for myself: […] The post Treat Yourself To A Luxury Expense To Make Investing Worthwhile appeared first on Financial Samurai.
I finally got around to updating my sharesight portfolio tracker with my latest quarterly Investment Bond contribution transactions (processed on 17 Feb). Currently the quarterly contribution is around $1,825 each quarter, and I will continue to increase this by 125% annually until it reaches $50Kpa (which is approximately what my ‘surplus’ tax-free self-funded pension income will be). In the
The Short Version: I bought about a dozen rental properties in the mid-2000s. I overleveraged, bought in rough neighborhoods, and had no idea how to actually forecast cash flow. I made every rookie mistake in the book. When 2008 hit, I got crushed from both sides… underwater properties and a job loss. It took years to recover. Even in normal times, landlording was exhausting. Tenant calls, bad property managers, mediocre returns after real expenses. There was nothing passive about it. Now I invest in passive real estate deals where operators handle everything. Better returns, zero headaches, and I actually get my time back. I used to be a landlord. I owned rental properties, dealt with tenants, managed contractors, and did all the things you’re supposed to do as a “real estate investor.” I hated it. That’s not the story you usually hear. Most real estate content online makes landlording sound like a straightforward path to wealth. Buy a property, rent it out, collect passive income, repeat. Financial freedom in a few simple steps. The reality was nothing like that. At least not for me. Here’s what actually happened, why I eventually sold my rentals, and what I do instead now. How I Got Into Rental Properties I fell into real estate by accident. After college in 2003, I had no idea what I wanted to do with my life. I ended up interning at a mortgage company, which led to a job in hard money lending. Suddenly I was surrounded by real estate investors, flippers, landlords… people who seemed to be making money hand over fist. This was the mid-2000s. The market was ripping. Everyone was getting rich in real estate, or so it seemed. I figured if they could do it, so could I. So I started buying rental properties. I bought about a dozen of them over a few years. I was convinced I was building wealth, building my future, doing the smart thing. I was 20-something years old, full of confidence, and had no idea what I was doing. The Mistakes I Made Looking back, I made every rookie mistake in the book. I overleveraged. I put as little down as possible on each property, stretched myself thin across multiple deals, and assumed the market would keep going up forever. I had no real cash reserves. No margin for error. I didn’t know how to forecast cash flow properly. I was running around thinking cash flow was just rent minus the mortgage payment. I had no concept of the 50% rule… the idea that roughly half your rent goes to non-mortgage expenses when you average out vacancies, repairs, maintenance, property management, and everything else that eats into your returns. I bought in rough neighborhoods because the cap rates looked great on paper. What I didn’t understand was that lower-income rental properties are a niche investment strategy that requires niche expertise. The turnover is higher. The property managers willing
Ten years ago, we bought our very first home — a 3-bedroom, 2-bathroom condo in the inexpensive city of Gainesville, Florida. And after living there ourselves for a while, it became our very first rental property investment — providing us with extra income as we traveled the world from Canada to Australia to Iceland. After what felt like a very successful decade of homeownership and landlording, we just sold that condo and ran the final […]
Can’t fit all your investments into your ISAs and SIPPs? Then you’ll reduce your tax bill by following the first rule of tax-efficient investing: Squeeze the most heavily taxed investments into your tax shelters first. Happily, the pecking order for maximum tax efficiency is clear cut for most people. Tax-efficient investing priority list Shelter your assets in this order: Non-reporting offshore funds Bond funds, money market funds, UK REITs and PIAFs Individual bonds Income-producing equities […]
Over three years later, and my Worth Bonds are worthless. I reported back in August 2022 that Worthy Bonds were having liquidity problems. Last month I received the following email: Hi Joseph, As of February 2nd, 2026, after exhausting all available debt-recovery and asset sale efforts, Worthy Peer Capital has determined that no further funds remain for distribution to bondholders. As a result, any securities held in this offering should at this time be considered […]
Continuing with our theme of cybersecurity, I read an article this week about a new software product for fraudsters. With this software, the user (a would-be thief) types in a URL of a genuine website, and when a target visits a selected scam URL, the software loads up an invisible browser window to collect, in real-time, all of the genuine website’s information, which it then passes through to the victim’s browser window. In other words, […]
I’ve been getting a lot of updates lately from operators I’ve invested with. And the tone has shifted. Not dramatically, but enough to notice. Distributions paused here. A refinance that didn’t go through there. Language that used to feel confident now feels careful. And here’s the thing. The properties are fine. Occupancy is solid. The markets are doing okay. On paper, nothing about the actual assets looks broken. But the deals are under stress. If […]
Image source: Amazon Key comics are comic books that are historically important to comic book industry fans and collectibles experts. The first appearances of Superman, Batman, or Spider-Man are key comics. The first time that major Marvel characters like Iron Man, Thor, and the Hulk combine to form the Avengers is a key comic. Pivotal storyline, character deaths, first work of famous creators, and so on, can make a comic a key comic. Another major […]
When I bought physical gold for the first time in 2024, it surprised some people — including myself who used to advocate Warren Buffett’s take on gold. Gold doesn’t generate income. It doesn’t compound. It doesn’t fit neatly into the discounted cash flow models I’d spent years studying. And yet, it felt inevitable. The Wrong Lesson First My first encounter with gold came during COVID-19. Markets were crashing. Governments were printing money at unprecedented scales. […]
🎙️Episode #477 – Your portfolio grew, but your freedom didn’t. Learn how to shift from “builder mode” to true freedom, and why more rentals and… The post Why Your Real Estate Wealth Still Doesn’t Feel Like Freedom appeared first on Coach Carson.
The post 2026 Canadian Dividend Aristocrats: Analysis, Performance, and Insights appeared first on Dividend Power. The 2026 Canadian Dividend Aristocrats are Canadian stocks that have grown dividends for 5+ years. There are currently 97 stocks on the list. However, five years or more of dividend growth does not by itself qualify a stock as a Canadian Dividend Aristocrat. A company must meet three criteria to be included on the list: Be a member of the S&P Canada […]